N-[(4-tert-butylcyclohexylidene)amino]-2,4-dinitroaniline | 54532-12-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[(4-tert-butylcyclohexylidene)amino]-2,4-dinitroaniline
• 英文别名: 4-tert-butylcyclohexanone 2',4'-dinitrophenylhydrazone；4-tert-butylcyclohexanone 2,4-dinitrophenylhydrazone；4-t-Butylcyclohexanone 2,4-dinitrophenylhydrazone；2,4-Dinitro-phenylhydrazon des 4-tert.-Butyl-cyclohexanon；4-tert.-Butyl-cyclohexanon-(2,4-dinitro-phenylhydrazon)；4-tert.-Butyl-cyclohexanon-(2,4-dinitrophenylhydrazon)；t-Butyl-4-cyclohexanon-2,4-dinitrophenylhydrazon
• CAS: 54532-12-6
• 化学式: C₁₆H₂₂N₄O₄
• 分子量: 334.375
• InChiKey: BZGORWGBDJVJTJ-ATVHPVEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.51
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  110.67
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-[(4-tert-butylcyclohexylidene)amino]-2,4-dinitroaniline 在 lithium aluminium tetrahydride 、 iodine monofluoride 作用下， 生成 1-叔丁基-4,4-二氟环己烷
  参考文献：
  名称：

  Conversion of the carbonyl group to CF2 using iodine monofluoride (IF)

  摘要：

  A novel method for the transformation of CO --> CF2 is described. The easily made hydrazone derivatives of the carbonyl moiety are reacted under mild conditions with IF prepared directly from the corresponding elements. Various hydrazones have been examined and compared with each other. Unsubstituted ones are usually the most suitable although they are not always easy to purify and store. N-Methyl- and N,N-dimethylhydrazones also give quite satisfactory results. The more easily made dinitrophenyl hydrazones (DNPs), semicarbazones, and tosylhydrazones also react, but the yields of the desired CF2 compounds are usually lower. Oximes could also be successfully reacted. The two main byproducts of the reaction are the parent carbonyl compounds, which can be recycled, and the alpha-iododifluoro derivatives. The latter upon treatment with LiAlH4 or Bu3SnH were reduced to the desired product, thus increasing the overall yields.

  DOI：

  10.1021/jo00015a024
• 作为产物：
  描述：

  3-(TERT-BUTYL)-1-(MESITYLMETHYL)-1H-PYRAZOLE-5-CARBOXYLIC ACID 在 N,N-二甲基丙烯基脲 、 偶氮二异丁腈 、 三正丁基氢锡 、 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 生成 N-[(4-tert-butylcyclohexylidene)amino]-2,4-dinitroaniline
  参考文献：
  名称：

  New Applications of 1,5-Hydrogen Atom Transfer Reactions: Self-Oxidizing Protecting Groups

  摘要：

  新介绍了三种保护醇的基团：邻溴苄基、邻溴（亚甲二氧基）苄基和邻溴三苯甲基。在还原条件下，用三丁基锡氢化物去除这些保护基团，同时将底物氧化，直接生成醛或酮。这种氧化过程是通过1,5-氢转移，随后发生β-碎片化完成的。例如，在0.001 M浓度下（80°C）用三丁基锡氢化物处理3-苯基-1-丙醇的邻溴苄基醚，直接生成3-苯基-1-丙醛。还介绍了在存在二级醇的情况下选择性氧化一级醇的应用。

  DOI：

  10.1055/s-1992-34173

文献信息

• A mild reductive conversion of oximes to ketones
  作者：Dennis P. Curran、Jan F. Brill、Donna M. Rakiewicz

  DOI：10.1021/jo00183a034

  日期：1984.5
• A Novel Carbonyl to CF2 Transformation Using BrF3
  作者：Shlomo Rozen、Eyal Mishani、Arie Bar-Haim

  DOI：10.1021/jo00090a002

  日期：1994.6

  This work demonstrates that BrF3 is very efficient in converting various carbonyls through their azines, oxime methyl ethers, or various hydrazones into the corresponding CF2 moiety.
• Rozen Shlomo, Mishani Eyal, Bar-Haim Arie, J. Org. Chem, 59 (1994) N 11, S 2918
  作者：Rozen Shlomo, Mishani Eyal, Bar-Haim Arie

  DOI：——

  日期：——
• CURRAN, D. P.;BRILL, J. F.;RAKIEWICZ, D. M., J. ORG. CHEM., 1984, 49, N 9, 1654-1656
  作者：CURRAN, D. P.、BRILL, J. F.、RAKIEWICZ, D. M.

  DOI：——

  日期：——